Flavone (CHEM003880)

Record Information
Version1.0
Creation Date2014-09-11 05:22:42 UTC
Update Date2026-08-19 08:47:11 UTC
Accession NumberCHEM003880
Identification
Common NameFlavone
ClassSmall Molecule
Description
Quercetin is a flavonoid that forms the "backbone" for many other flavonoids, including the citrus flavonoids rutin, hesperidin, naringin and tangeritin. In studies, quercetin is found to be the most active of the flavonoids, and many medicinal plants owe much of their activity to their high quercetin content. Quercetin has demonstrated significant anti-inflammatory activity because of direct inhibition of several initial processes of inflammation. For example, it inhibits both the manufacture and release of histamine and other allergic/inflammatory mediators. In addition, it exerts potent antioxidant activity and vitamin C-sparing action.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Plant Toxin
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Phenyl-4-benzopyronChEBI
2-Phenyl-4-chromoneChEBI
2-Phenyl-4H-1-benzopyran-4-oneChEBI
2-Phenyl-4H-benzopyran-4-oneChEBI
2-PHENYL-4H-chromen-4-oneChEBI
2-Phenyl-gamma-benzopyroneChEBI
2-Phenylbenzopyran-4-oneChEBI
2-PhenylchromoneChEBI
FlavonChEBI
2-Phenyl-g-benzopyroneGenerator
2-Phenyl-γ-benzopyroneGenerator
Flavone, 14C-labeledMeSH
Chemical FormulaC15H10O2
Average Molecular Mass222.239 g/mol
Monoisotopic Mass222.068 g/mol
CAS Registry Number525-82-6
IUPAC Name2-phenyl-4H-chromen-4-one
Traditional Nameflavone
SMILESO=C1C=C(OC2=CC=CC=C12)C1=CC=CC=C1
InChI IdentifierInChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H
InChI KeyVHBFFQKBGNRLFZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • Flavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Placenta
  • Prostate
  • Spleen
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point100°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0082 g/LALOGPS
logP3.54ALOGPS
logP2.97ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)15.63ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.97 m³·mol⁻¹ChemAxon
Polarizability23.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIn studies, quercetin is found to be the most active of the flavonoids, and many medicinal plants owe much of their activity to their high quercetin content.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB07776
HMDB IDHMDB0003075
FooDB IDFDB006784
Phenol Explorer IDNot Available
KNApSAcK IDC00001040
BiGG IDNot Available
BioCyc IDCPD-8485
METLIN ID3359
PDB IDNot Available
Wikipedia LinkFlavones
Chemspider ID10230
ChEBI ID42491
PubChem Compound ID10680
Kegg Compound IDC15608
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11370674
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12063116
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17347140
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18596412
5. Cummings J, Kerr DJ, Kaye SB, Smyth JF: Optimisation of a reversed-phase high-performance liquid chromatographic method for the determination of flavone acetic acid and its major human metabolites in plasma and urine. J Chromatogr. 1988 Sep 23;431(1):77-85.
6. Choi MH, Kim KR, Hong JK, Park SJ, Chung BC: Determination of non-steroidal estrogens in breast milk, plasma, urine and hair by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2002;16(24):2221-8.
7. Cai H, Steward WP, Gescher AJ: Determination of the putative cancer chemopreventive flavone tricin in plasma and tissues of mice by HPLC with UV--visible detection. Biomed Chromatogr. 2005 Sep;19(7):518-22.
8. Barrellier MT: [Lymphedema: is there a treatment?]. Rev Med Interne. 1992 Jan-Feb;13(1):49-57.
9. Sengupta B, Uematsu T, Jacobsson P, Swenson J: Exploring the antioxidant property of bioflavonoid quercetin in preventing DNA glycation: a calorimetric and spectroscopic study. Biochem Biophys Res Commun. 2006 Jan 6;339(1):355-61. Epub 2005 Nov 15.
10. Weiss RB, Greene RF, Knight RD, Collins JM, Pelosi JJ, Sulkes A, Curt GA: Phase I and clinical pharmacology study of intravenous flavone acetic acid (NSC 347512). Cancer Res. 1988 Oct 15;48(20):5878-82.
11. Alonso M, Tamasdan C, Miller DC, Newcomb EW: Flavopiridol induces apoptosis in glioma cell lines independent of retinoblastoma and p53 tumor suppressor pathway alterations by a caspase-independent pathway. Mol Cancer Ther. 2003 Feb;2(2):139-50.
12. Ching LM, Joseph WR, Crosier KE, Baguley BC: Induction of tumor necrosis factor-alpha messenger RNA in human and murine cells by the flavone acetic acid analogue 5,6-dimethylxanthenone-4-acetic acid (NSC 640488). Cancer Res. 1994 Feb 15;54(4):870-2.
13. Kim SJ: Effect of biflavones of Ginkgo biloba against UVB-induced cytotoxicity in vitro. J Dermatol. 2001 Apr;28(4):193-9.
14. Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71.